Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: sissyboy1212 on November 16, 2024, 06:52:37 PM
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This is a short story I started a while back. Just thought I'd finish it off. It's about seven short chapters. Here is the first one, and I'll post the others over the next few days as I proofread them. Hope you enjoy and Happy November!
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Part 1
“Come on Jamie!” Susan Padgett chided her 13-year-old son, “and stop your pouting!”
Grumpily, Jamie Padgett got out of the car and followed his mother toward Mrs. Green’s large house. He wasn’t happy to be here, and he wasn’t happy to be wearing these clothes either.
He was nattily dressed in a starchy short sleeve dress shirt and a baby blue bowtie with little white paisleys on it. He wore a dressy pair of scratchy light blue slacks and a narrow black leather belt. He was wearing his black tasseled penny loafers with baby blue dress socks that had white paisleys to match his tie. His mother had combed his medium length brown hair neatly and sprayed it down to hold it in place. He felt like a total dork, and he was grumpy because his mother was dragging him along again to her boring book club meeting like a little boy. For crying out loud, he was a teenager now!
She had made him come with her to the last meeting two weeks ago as well right before his 13th birthday because she couldn’t find someone to stay with him. Although he complained that he was old enough to stay by himself a few hours at home, Susan was reluctant to loosen the apron strings on her new teenager. At least the last time, he had been able to wear more casual clothes and play with his friend Bobby who was Mrs. Green’s 13-year-old son. Bobby and Jamie were in the same grade at school.
Bobby was more of an instigator, while Jamie was a follower, and the boys had gotten so boisterous that they had disrupted the last meeting with their loud and rowdy antics. First, they had annoyed Bobby’s 18-year-old sister Daphne while she was trying to study for the SAT. That had resulted in some yelling and commotion, and Mrs. Green had to leave the book club to go upstairs and kick the boys outside so Daphne could concentrate. Then, Bobby had caught a frog in the garden and let it loose in the great room while the ladies were discussing their book, tracking a fair amount of mud on the carpet in the process. Although Jamie hadn’t really done anything but watch, he had laughed along while the ladies scrambled out of their chairs. Diane Green had not been happy with her mischievous son, and Susan Padgett had chided her own son for letting himself be influenced in such a misbehaving way.
“If Bobby Green jumped off a bridge, would you jump too?!” she had asked rhetorically.
Today, she had decided that Jamie would sit beside her in the book club instead of being left to find trouble on his own, and she had made sure he was dressed appropriately. “We always dress nicely for our book club meetings,” she had told him earlier as she fixed his bowtie. “There,” she had said with a pleased look, “you look like a perfect little gentleman.”
“And don’t worry, your little partner-in-crime Bobby will be there too!” she had added with some amusement.
They reached the front door and rang the bell. Soon Mrs. Green opened the door and welcomed them in. “So good to see you again, and Jamie, don’t you look nice today!” she said pleasantly.
Turning to Susan, she remarked with a curious smile, “I feel sure the boys will stay out of mischief this time!” Continuing, she added, “I know my Bobby very well, and unfortunately he can be quite the troublemaker sometimes. I’m sorry he has been leading young Jamie here into misbehavior!” Then with a slight giggle, “but I think you’ll see I’ve found an effective way to adjust his attitude!”
This mysterious comment made Jamie somewhat confused and a little wary, especially when he saw his mother respond with a knowing smile.
“Thank you, Diane! I’m sure you have things well in hand by now, and I think today will provide a good incentive for Jamie to stay on the straight and narrow too!” his mother said.
“Come along then,” Mrs. Green said pleasantly, “I think you’re the last to arrive so we can get started.” Nervous now, Jamie followed Mrs. Green and his mother into the great room where there were already almost twenty ladies sitting around several small white tables. As he and his mother took the last chairs around one of the tables, Jamie realized that he was the only boy there, and he felt like all the ladies were watching him as they sat down. Bobby was nowhere to be seen.
Jamie shifted uncomfortably in his seat.
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A very nice start, I already have an image planted in my head as to what is going to happen. I hope it turns out that way. Waiting with baited breath for the next part.
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I hope it goes the way I think it will, but wouldn’t be sad if it didn’t. This has the potential to go in many different directions which I like. Great start
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Interesting start. Sounds like Bobby and Jamie are going to be very good little boys from now on. Look forward to continuation
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PART 2
“Before we start,” Mrs. Green began, “I must apologize again for all the ruckus at our last meeting. Let me assure you that I’ve taken measures to ensure we will have a much more enjoyable time today.” Nodding to Jamie, she said, “as you can see young Master Jamie here is going to sit nicely with his mother and get exposed to some literary culture. He won’t be pulled into more of Bobby’s, shall I say, shenanigans.”
Jamie reddened as the ladies stared at him again, and he heard a few quiet titters. He got the overwhelming sense that they all enjoyed seeing him chastened like a little child. Although he was a teenager now, it made him feel so immature to be dragged along like this by his mother. Right on cue, his mother patted his knee in a very maternal way, as if to reassure him and everyone else that she had her child firmly in hand.
“And I’m thrilled to report that my little Bobby has begun to turn over a new leaf, so to speak. In fact, he is so regretful of his disruptive behavior last time that he practically insisted on helping me host today’s book club meeting to make amends!” she said with a twinkle in her eye. “I think you’ll all be amazed at his turnaround!”
With that, she called out toward the great room’s open door, “Daphne, would you bring Bobby in please so we can ‘re-introduce’ him to the ladies?”
Baffled, Jamie wondered what was going on, but none of this sounded good. He couldn’t imagine anything that would make Bobby want to help his mother with her stuffy book club. A bit unsettled, he sat wondering what was going to happen next.
Then, Jamie heard Daphne’s voice outside the door in what amounted to a stage whisper, “Go on! Stop dawdling and get in there!” It was clear she was giving her little brother instructions.
Moments later, an obviously mortified Bobby was shepherded into the great room by his big sister. Daphne wore a pleased look as she nudged her little brother along. Despite his penchant for finding trouble, Bobby was still on the small side and his big sister practically towered over him. The 13-year-old’s face was beet red as he stepped gingerly through the door, and all the ladies murmured and giggled when they saw how he was dressed.
Jamie’s jaw dropped as he watched Bobby take slow nervous steps to the front of the room with his watchful sister close behind. He couldn’t believe his eyes as he took in the outfit Bobby was wearing.
Jamie cringed himself as he felt embarrassed for the both of them.
Blushing brightly, Bobby Green stood meekly in front of all the ladies of the book club. The teenaged boy was dressed just like a prissy little girl! Bobby wore a gorgeous baby blue party dress that looked like it was designed for a toddler. It was made of a soft satiny material and sported the cutest short puffy sleeves. The puff sleeves ballooned up around his narrow shoulders before being gathered with elastic at the top of his slender bare arms. His dress also boasted delightfully layered tulle accents that added such wonderful feminine accents to the voluminous look. Delicate lace embroidery adorned his gauzy bodice, and his dress gathered sweetly at his waist with a wide white sash tied into a fancy bow.
From the waist down, the cringing adolescent’s skirt flared out ostentatiously. The three-tiered skirt had a generous helping of dainty ruffles, and it was obvious Bobby was wearing a very full tulle petticoat underneath. Aghast, Jamie could see what looked like multiple layers peeking out underneath Bobby’s short skirt which reached only to the middle of his bare thighs. Bobby’s beautiful frock boasted even more lovely embroidered white lace gaily decorating the gauzy hem of the skirt.
On his feet, Bobby wore a pair of very frilly white ankle socks with lovely layers of puffy tulle ruffles encircling his ankles. A shiny pair of black Mary Janes were buckled on his feet to complete his adorably childish outfit. Bobby’s girlish shoes clacked daintily on the tile floor as he minced along.
Jamie watched in horrified amazement to see his friend turned into such a sissy before his eyes. Jamie noticed that Bobby’s eyes were slightly red as if he had been crying.
Then, Daphne spoke again to her charge, “Go ahead, Bobby, just like we practiced!”
After a slight hesitation, Bobby held the hem of his skirt gingerly and gave a shaky curtsey to the assembled ladies. When they saw the sissified boy perform such a feminine gesture they spontaneously burst into some soft clapping in appreciation.
The ladies then made various comments such as “How lovely,” “So darling,” and “I love your party dress Bobby!” The tittering started again.
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Part 3
With a pleased look, Mrs. Green addressed her feminized teen. “Bobby, don’t you have something to say to the ladies?”
Nervously, heeding his mother’s direction, Bobby spoke in a small wavering voice, “Yes Ma’am. I’m, uhh… I’m so very, very sorry for the trouble I caused at your last meeting.” Then after another painstaking pause, he added, “I am… delighted to help host your book club today.” It was obvious he had rehearsed his lines. Cringing even more, he shifted his feet uncomfortably as he stood at the center of attention.
“Give us a twirl, dear, so the ladies can see your pretty dress,” Mrs. Green instructed her son.
Already on pins and needles, Bobby complied meekly and spun around for the group. When he twirled hesitatingly, his bouncy skirt practically floated up, and Jamie could see even more white feminine ruffles underneath!
“Careful little brother,” Daphne warned with a giggle, “or else you’ll show everyone those pretty rhumba panties you’re wearing.” At this remark, Bobby’s face turned an even deeper shade of red.
“That’s right, honey, we must maintain our modesty,” Mrs. Green added.
“Panties?!” Jamie recoiled at the thought. “He’s even wearing panties?!” Jamie shuddered as Bobby just looked more miserable.
At this point, Bobby finally seemed to notice that Jamie was also in the room watching every aspect of his abject humiliation. Bobby locked eyes with Jamie in a look of pained embarrassment, and for some reason this made Jamie feel even worse. Jamie reddened himself and looked down. This was horrible to watch!
As if on cue, Mrs. Green spoke again to the group, “honestly, I tried all sorts of things to improve Bobby’s behavior, but nothing seemed to take hold.” She explained, “then, after the fiasco at our last book club, I decided to give petticoating a go, and I couldn’t be more pleased with the results!” She went on, “of course Bobby was less than thrilled about it at first, to put it mildly, but I was adamant!” Gesturing to Daphne, she added, “and Daphne was quite eager to lend a hand!” She continued, “Getting him into a dress that first time was quite the job, but Bobby soon discovered in no uncertain terms that he's not too old for a spanking!” Mrs. Green concluded triumphantly, “and once he realized that I meant it when I said I would send him to school in dresses if he didn’t get on board with the program, he quickly changed his tune!”
Several of the ladies murmured in approval. Jamie heard one of them remark, “Well this is certainly a welcome change!”
“Since you all had to suffer Bobby’s mischief at our last meeting, I thought it might be informative for you to watch as we add some nice details to complete his look today. They say that in order for petticoating to be most effective, it must be extremely thorough and uncompromising! The idea is to ensure that there is nothing boyish or masculine left for the petticoated boy to latch onto during the process. When I put Bobby into his ‘petticoat time,’ I take a total immersion approach! This sets the proper conditions for true behavior modification to take place!”
The ladies nodded in agreement as they listened to Mrs. Green speak about her new system of discipline. They all seemed pleased to see the little troublemaker get his comeuppance! Bobby, on the other hand, looked defeated and crestfallen.
“By all means, go ahead,” one of the ladies said cheerfully.
With a smile, Diane Green nodded appreciatively in response, “of course!” Speaking to Daphne, she said, “Daphne dear, would you bring that stool up here?”
“Certainly Mom,” Daphne replied. She moved a small stool to the front of the room and gestured for her petticoated little brother to take a seat.
Very carefully, Bobby gathered the layers of his skirts and sat down as he was told. He kept both his hands on his lap in a futile attempt to hold his frilly dress down. He clasped his legs together tightly as he tried to preserve some shred of modesty, and the multiple layers of his underskirts rustled audibly.
Jamie watched this entire sequence with a mixture of disbelief and discomfort. To see his friend so thoroughly sissified was almost too much to bear. By now, it was increasingly clear that his mother had known about this all along, and he was already beginning to worry that he might be next. He gulped nervously at the thought.
Jamie saw Mrs. Green pick up a small box, but before he saw what it was for, he heard his mother’s voice. His attention was immediately diverted.
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Jaime has the right to be nervous. He is seeing his future in front of him
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Wow! How exciting!
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I'm really enjoying this sweet story.
Thank you for sharing.
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Part 4
“Oh Diane,” Susan spoke up, “I was thinking that it might be nice for Jamie to help you with Bobby’s finishing touches.” She elaborated, “after all, Jamie caused his fair share of problems last time too.”
“That’s a wonderful idea Susan!” Diane agreed. “Why don’t you come up here with me Jamie?”
Jamie looked at his mother in silent protest, but she simply smiled back and said, “Go ahead, dear. It will give you a chance to get a closer look at Bobby’s dress. I’m sure you must be curious!” Then she added, “you seemed to follow along with him so eagerly before; this will give you another opportunity to ‘team up’ with him!”
Horrified, Jamie realized that he’d better do as his mother wanted. The unspoken threat was that he might find himself in a dress too! Slowly, he got up from his chair and walked over to Mrs. Green and Bobby. The two boys locked eyes again. Bobby seemed even more humiliated.
“Here you are dear,” Mrs. Green said as she handed him a very elaborate blue and white hairbow. Jamie held the girly hairbow very tentatively as he stood next to his humiliated classmate.
Noticing how gingerly he held Bobby's hairbow, Mrs. Green said teasingly, “It’s not going to bite you dear!” Several of the ladies chuckled again at that.
With Mrs. Green’s guidance, Jamie stepped in front of his friend and fastened the oversized hairbow in Bobby’s curly blonde hair. Jamie’s hands trembled due to the awkwardness of the situation as he leaned over his classmate so closely. Bobby’s hairbow had a large alligator clip underneath to hold it firmly in place, but Mrs. Green insisted that Jamie add a couple of additional clips to hold it tightly in place for “extra security.” Being forced to take such an active and personal part in his friend’s sissification was an awful feeling, and both boys had a swirl of emotions wash over them. When Jamie finally got the hairbow placed to Mrs. Green’s satisfaction, he stepped back immediately. Now, thanks to his classmate, Bobby wore the darling blue satin hairbow with lovely white lace accents in his curly blonde hair. He looked even more girlish and adorable now.
“It’s a shame his hair is still too short for more suitable styling,” Mrs. Green observed, “but I’ve decided that he’ll grow it out, so soon we’ll be able to put him in some proper curls or pigtails!”
“Oh, even with the shorter hair, he’s already so precious with that gorgeous hairbow!” Jamie’s mother exclaimed. Several of the ladies nodded in agreement.
It was then that Jamie realized how similar the colors of his outfit were to Bobby’s party dress. Their mothers had coordinated their clothes! Then he belatedly became aware that Daphne had been taking pictures the whole time with her phone! He blanched at the thought of any of his other friends from school seeing photos of this. He and Bobby would never live it down! Jamie wanted nothing more now than to run back to his chair and get as far away from his girlified friend as possible, but he quickly found out he was not done yet.
Daphne put her phone down and next and handed Jamie a tube of lip gloss. “Here you go, Jamie” she said sweetly, “Bobby needs a touch of color to brighten up his look!” Daphne proceeded to guide Jamie in applying a lovely coat of understated pink lip gloss to his friend’s lips. She had her little brother pucker up and then supervised closely as Jamie was forced to apply Bobby’s lip gloss for him. It was an uncomfortably intimate thing to do, and both boys’ stomachs jumped repeatedly as Bobby’s lips were carefully coated with the creamy pink lip color. When Jamie was finally done, Daphne instructed Bobby to roll his lips together several times to get his lips thoroughly coated. Then, she had Jamie get a tissue and lightly blot Bobby’s lips to remove any excess. Jamie was left holding the tissue with his friend’s pink lip print on it. It nearly made his skin crawl. Meanwhile, Bobby’s lips were now a darling shade of pale pink.
“That’s perfect,” Daphne said with approval, “Your lips are so kissable now little brother!” She added, “and the good news is that’s a long-lasting lip stain, so that color should last a good day or two!” Addressing Jamie, she asked teasingly, “perhaps you’d like to try some too?” Instinctively, Jamie shook his head furiously.
At this point, Jamie realized that his mother had her phone out as well. Every bit of this horror show was being captured in photos! Then his mother spoke again, seeming a bit carried away in the moment, “Oh why not Jamie? You ought to get a little taste as well. After all, what’s good for the goose is good for the gander!”
Caught by surprise and seemingly unable to speak, Jamie stood motionless for a moment. Before he fully comprehended what was happening, Daphne had grabbed his chin and began putting the pink lip gloss on him too! It felt so slick and creamy on his lips, and it had a sweet strawberry taste. He felt so helpless and emasculated in that moment. She had him roll his lips just like Bobby had done, and then she had Bobby blot Jamie’s lips with a tissue just like he had done to Bobby moments ago. Then, Daphne picked up a small hand mirror and held it so Jamie could see the results. Jamie gawked in dismay as he saw how girly he looked with his fresh pink lip gloss!
“Aww,” Daphne said with a little chuckle, “that’s adorable, Jamie! Now you’re just as sweet and kissable as my darling little brother!”
Bobby looked as if he wanted to cry, and Jamie realized he was still holding the tissue with Bobby’s pink lip prints between his fingers. Jamie wanted to sink into the floor.
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Now that is the ultimate humiliation, being forced to sissify your friend than having it done to you
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Thanks! The added embarrassment of having to actively participate just seems right for this story ;)
Making some small revisions on the next part now to post soon.
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Made slight edits to the end of Part 4. Will post Part 5 later today :)
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Part 5
“Wonderful!” Mrs. Green spoke again. “Your lip gloss is just precious boys! It looks so cute on you both!” Then, she put her hands lightly on Bobby’s shoulders as she presented him again to the ladies. “I think our junior hostess is ready now,” she said happily. “Turning to Jamie, she added, “Thank you Jamie, it seems you might have a natural affinity for petticoating!”
Lightly squeezing her son’s shoulder, she asked leadingly, “Bobby, don’t you have something to say to Jamie?”
With a defeated look, Bobby said softly, “Th- Thank you Jamie for helping me with my… my hairbow and lip gloss.”
Gulping, Jamie said quietly, “Uh sure… you’re welcome, Bobby.” This was a nightmare. As he gawked at Bobby’s pretty pink lips, it crushed him to know that his looked the same way.
Then Jamie’s mother spoke again, “Diane, if you don’t object, we brought along another little surprise for Bobby that I think you’ll approve of.” Continuing, she said, “I think it will be especially appropriate for serving the refreshments.” Then she added, “Come here Jamie.”
Mrs. Green seemed delighted, and she immediately agreed, “Why thank you Susan! Of course!”
Almost in a daze, Jamie obeyed his mother. She reached into her purse and retrieved a small white satin bag tied with a white ribbon. “Go take this gift over to your little friend,” she directed.
All the ladies watched expectantly at the sight of the smartly dressed young teen in the bowtie taking the delicate looking package to his sissified friend. After the disruptions at the last book club, the ladies seemed to take particular satisfaction in seeing these young whippersnappers get their due!
Jamie handed the girly satin bag to Bobby and muttered, “Uh, here you go.” He wanted it out of his hands as rapidly as possible. It was almost as if he believed the girlishness was contagious, and he was going to catch it if he got too close.
Dejected, but having no other option, Bobby untied the delicate ribbon and opened the satin bag. He was rewarded with a lovely pair of translucent white lace gloves. He saw his mother gesture to him, and he reluctantly pulled them on. The stretchy gloves were decorated with an exquisite lace pattern in a floral print, and they sported extra frills around the elasticated wrist openings. The lacy creations had wide white ribbons dangling from the wrists, and Bobby held his daintily gloved hands out in front in the most girlish way.
“Those were labeled as ‘tea party gloves’ and I think they are fitting for the occasion,” Susan Padgett explained with a grin. She added, “they are a small gift to you from Jamie and me in honor of your 'new start'!” Then she instructed, “Jamie, why don’t you help Bobby tie the bows on his gloves properly?”
Understanding now what the ribbons were for, Jamie cringed again but obeyed his mother after a moment’s hesitation. Reluctantly, he took Bobby’s hands one by one and tied the loose ribbons into the cutest little bows around each wrist. Once again, he felt very flustered having to take such a direct role in his classmate’s feminization. Mrs. Green helpfully supervised Jamie’s efforts to make sure he got the fussy bows nice and even.
“Well, those are just darling!” Mrs. Green agreed as Jamie finished, “and they’re perfect! Thank you so much!” Then she leaned over and whispered something in Bobby’s ear.
Bobby cringed noticeably as he echoed his mother defeatedly, “Thank you for my gloves, Mrs. Padgett… and Jamie too.” Then he looked back at his mother almost pleadingly, and she nodded back at him in response.
An instant later, Jamie was flabbergasted when Bobby abruptly stepped next to him and gave him a little peck on the cheek! Jamie recoiled instantly, and both boys blushed even more brightly. Jamie was shocked beyond belief. He opened his mouth and closed it without saying a word, and his emotions swirled. Unbeknownst to him, the sissy kiss left a faint but clearly visible pink lip print on his left cheek.
Daphne piped in, “Aww isn’t that sweet?” as several of the ladies murmured in agreement. Then, Daphne added teasingly, “It looks like someone has a crush on you, Jamie!”
At that, Jamie’s tummy did a backflip, and he felt his face heat up even more! He stared wordlessly at Daphne, unable to muster a response. Then, he looked at Bobby who was staring down at the floor in shame and nervously fidgeting with the hem of his toddler-ish satin party dress. Jamie returned his gaze to Daphne who let out a little giggle and playfully wagged her finger at him.
Looking very amused, Mrs. Green said, “Let’s start our meeting and have our refreshments, shall we?”
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The only thing more humiliating for Jaime and Bobby right now would be for them to “excited” in their pants and being caught, as every male knows at that age, anything can “excite” it.
I am loving this story
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Thanks! You might enjoy some of the future chapters then ;) that type of thing usually shows up at some point in most of my stories.
Still tweaking the ending but will post the next part later today.
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Part 6
Jamie sat back down beside his mother with great consternation as all the ladies began discussing their current book. It was something (incredibly boring to him) about two middle-aged women who took a trip to Europe together. The two shared countless empathetic and empowering moments with each other on their journey, and they also consumed copious amounts of wine along the way. Jamie fidgeted restlessly in his seat until he eventually saw Daphne usher Bobby out toward the kitchen… presumably to get the snacks. Jamie was beside himself. All the stuff the ladies were talking about was tedious, but he was still so nervous and uneasy due to the afternoon’s events. He fidgeted noisily in his seat until his mother shushed him with a finger to her lips.
Soon, Bobby and Daphne reappeared with trays of snacks. Daphne put her tray down on a side table and then went over to Mrs. Green and whispered in her ear. Bobby put his tray down as well and stood skittishly next to the table, holding the sides of his skirt with his lace-gloved hands.
Despite Jamie’s unease, he was inexplicably captivated by the spectacle of Bobby’s petticoating. He couldn’t help himself! It seemed to Jamie that every little movement Bobby made caused his puffy skirt to bounce up and down. Unable to look away, Jamie was mesmerized watching Bobby’s dress flit and flutter so girlishly. Jamie suddenly realized with chagrin that he was stiff “down there” and began to fidget even more. He felt so jumpy and anxious as he felt his face warming again! Then he was abruptly snapped out of his daydreaming.
“Excellent idea, Daphne” Mrs. Green said to her daughter. Mrs. Green called over to Jamie’s mother, “Susan, do you suppose Jamie would mind helping Bobby serve the refreshments? He could pour the tea.”
“Of course, he’ll be happy to help!” Susan immediately replied. “He can’t seem to keep still anyway!” Reaching into her purse she added, “and now I know what to do with this other set of gloves! There were two sets in the package!”
In short order, she directed her son, “stand up and put out your hands dear!” She added quickly, “if you’re going to serve the ladies today, then it’s better you wear gloves as well.” In no time, Jamie was horrified to find himself wearing an identical pair of the prissy lace gloves that Bobby was wearing. He felt like such a sissy… he couldn’t even imagine what Bobby must be feeling. The tingling in his pants got more pronounced!
Then, Mrs. Green insisted that Bobby return the favor and tie Jamie’s ribbons for him. Grimacing, Jamie held out his hands while his charmingly frocked classmate secured the ribbons into cute little white bows. Jamie felt so strange as Bobby tied the ribbons on his gloves. Inevitably, Bobby’s springy skirt brushed Jamie repeatedly as his petticoated classmate fashioned the charming little bows around his wrists. As Bobby carefully knotted the ribbons, Jamie’s tension grew greater still. The little tent in his pants started to show!
Jamie’s pulse accelerated, and he was almost in a daze as he stared ruefully at his girly lace gloves. The intricate floral pattern in the lace looked so foreign and feminine on his hands. Then Daphne spoke up behind him, “you should wear this too Jamie!” Before he realized what was happening, Daphne dropped a white apron over his head and began tying it snugly around his waist. “I was going to dress Bobby in this, but I just couldn’t bear to cover up his precious outfit.” As Daphne meticulously straightened his apron, it was obvious she had noticed his little protuberance. “You, on the other hand, seem like you could use some covering up down there!” Giggling out loud as she finished, “well don’t you just look darling!” She shot a knowing look at Jamie, and then she called teasingly to her brother, “I think Jamie likes your dress, Bobby!”
Humiliated, Jamie looked down to see that Daphne had put him into a very frilly white apron. It had elaborate lace detailing with adorable baby blue trim. The ruffled straps fluttered gaily over his shoulders, and the whole thing felt so girlish. The worst thing was that his fluffy new apron only served to exacerbate his little “situation.”
Meanwhile, his mother beamed as she examined her son in his delicate lace gloves, frilly apron, and sweet pink lip gloss. His cute little bowtie looked almost feminine now that it was framed so prettily by his apron straps! It was amazing what a few little touches did to sweeten his appearance.
Under Daphne’s watchful eye, the pair of blushing boys in their matching outfits began serving the tea and finger sandwiches. While the ladies discussed their book, the boys meekly moved from table to table. At each table, Bobby had to bring over the little plates of sandwiches resting on white paper doilies. One by one, the petticoated teenager carefully placed the small plates on each table. Then, he stepped back demurely and concluded the presentation with another charming little curtsey. It was obvious he had practiced his little routine.
Next, Jamie would follow and pour tea for all the ladies to drink. Jamie was very conscious of the stretchy feel of his lacy gloves and the poofiness of his apron. The two boys couldn’t help but brush repeatedly against each other as they moved around in such close proximity. This ensured Jamie stayed in a constant state of bother as he served the tea. Poor Bobby, meanwhile, was in a perpetual battle to keep from showing his panties, and the layers of his skirt rustled ceaselessly with every little movement.
All the ladies seemed to light up as these formerly misbehaving boys made their little stop at each table. To the boys’ chagrin, more than one remarked that they made such a “cute little couple!”
When they were done serving, Daphne had the boys sit back down with their mothers. Since Susan and Diane were at the same table now, the boys sat next to each other in between their mothers. Their chairs were so close together that Bobby’s voluminous party dress practically overflowed onto Jamie’s lap as well, brushing him repeatedly in the most unnerving way. Jamie could only imagine how the multiple layers of tulle must be constantly tickling Bobby’s bare thighs. Jamie could almost feel Bobby’s girlishness soaking into him as if by osmosis, and his agitated state continued mercilessly.
At one point, Jamie caught Bobby’s eye and began to whisper to his classmate, “how did…?” But almost immediately, he was cut off with a pointed shush from his mother. She shot him a warning look to be silent, and she held her finger to her lips. For his part, Bobby just shook his head and quickly looked away. The charming hairbow clipped in Bobby’s curly hair seemed to exaggerate every little movement of his head. The minutes slowly ticked by.
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Poor Jaime. I have a feeling he is going to explode soon. This has been an amazing story, and cannot wait to see what the next humiliation is for the two of them.
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Shame it will have only 7 parts.... its one of the beat stories i ever read!!!
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Thank you :)
I have been reworking the ending so it will likely be 8 parts now. Plus I had an idea for an epilogue.
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I just love where you made the plot for Jamie while.he is sissy and dressed as sissy but aissy boy in very sissy boish attire. Its special and from some.point of.view even more degrading and sissifying then total girly wear. The way that he is reluctantly participate in the sissification of his friend is just art. Thanks!!!!!
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You have a very good story going. I have a funny feeling that Jamie is going to have his own petticoat experience very soon. Keep going and run with this story. You have a masterpiece going.
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Part 7
At long last, the ladies reached the end of their book discussion. The whole time, Jamie and a very jittery Bobby had sat in silent misery while the discussion droned on and on. As the ladies finished up, Daphne nudged the boys up from their seats. Jamie was on edge again but also morbidly curious about what was next. It appeared they would have to do more “hostess” duties, but he had no idea what they would be. Bobby, on the other hand, had a look of dread on his face as if he had been expecting this.
“We have some little goodies for you to take home, ladies. Please enjoy the sweets!” Mrs. Green explained. Under Daphne’s supervision, Jamie and Bobby handed out small packages of candies to all the ladies. The candies were wrapped up in pink mesh pouches and tied off with curly pink ribbons. All the pretty little packages were tastefully arranged in a white wicker basket trimmed with fussy pink ribbons. Jamie was assigned the task to carry the dainty basket full of treats around to each table. For each lady in the room, Bobby would then retrieve one of the little pink bags from Jamie’s basket and prissily present it. All the ladies marveled at how darling and well behaved the boys were contrasted with their last meeting. Bobby got many more compliments about how precious he looked as he minced around the room. Jamie also got his fair share of comments about his pretty apron.
Jamie hated being part of this whole scene. He wanted to talk to Bobby to find out how all this had happened, but he wanted most just to get away! At the same time, Jamie found it almost impossible NOT to look at Bobby as he skittered delicately about in all his sissified glory. Once again, he found himself staring at Bobby’s darling hairbow that he himself had pinned in place. Bobby’s shiny Mary Janes click-clacked on the floor with each step, and the layers of his billowy skirt were constantly floating up. Jamie winced every time he saw Bobby’s plump pink lips and remembered how uncomfortable it was to put lip gloss on his newly petticoated classmate. It also reminded him that his lips looked the same way after he had been forced to share Bobby’s lip gloss. This whole afternoon had been unsettling and surreal! Jamie soon found out there was one last matter on the agenda. It was excruciating to watch.
“Before we close, Bobby has another little treat for us. He’s been in his dresses all week to prepare for his hostess duties today,” Mrs. Green began, “and rest assured that he doesn’t just laze about the house once he is frocked and petticoated!” She explained, “he’s had quite a full schedule of household chores, and I’ve ACTUALLY got him doing his homework for once!” She added, “I also set aside ample time for him to practice his etiquette and deportment.” She continued, “Daphne even made the helpful suggestion that he could practice serving refreshments with some of her old dolls, so he’s put on some of the cutest little tea parties under her supervision!” She concluded, “and Daphne also squeezed in time to teach him a charming little song. I can’t tell you how excited he is to sing it for us!”
Incredulous, Jamie watched as Bobby walked sheepishly back to the front of the room. Bobby’s face was bright red again. It soon became clear that this is what he had been dreading the most. Then, Daphne grabbed Jamie’s hand and led him to a chair next to her. They sat down right in front of Bobby. “I just know you want a front row seat for your sweetheart’s performance, Jamie,” she said teasingly. Jamie blushed again and Bobby looked miserable. Daphne hit a button on her phone, and some chords of piano music began to play over a pair of wireless speakers. Nearly in anguish, Bobby looked helplessly at his mother, but she just smiled wryly and made a hand gesture for him to proceed.
Squirming in discomfort himself, Jamie thought that he vaguely recognized the tune from somewhere, but he couldn’t place it. Sitting next to him, Daphne began to mouth the words for her petticoated brother and coach him along. After a few chords, Bobby started to sing in a small, wavering voice. When Jamie heard him sing the first few words, it hit him.
“On The Good Ship Lollipop
It's a sweet trip to a candy shop
Where bon-bons play
On the sunny beach of Peppermint Bay”
“Oh my God,” Jamie thought with amazement. “He’s singing that Shirley Temple song!” Jamie watched dumbfounded as his furiously blushing classmate sang several verses of “The Good Ship Lollipop.” If that wasn’t enough, he was also performing a whole routine of hand motions and childish gestures to go along with the juvenile lyrics! His layered skirt bounced up over and over again to expose his petticoat and rhumba panties as he gesticulated girlishly. Reaching the last verse, Bobby sang,
“On The Good Ship Lollipop
It's a night trip, into bed you hop
And dream away
On The Good Ship Lollipop
You'll awake with a tummy ache!”
When Bobby sang, “…and dream away,” he put his palms together sweetly against his cheek as if he was going to sleep. Then, when he sang “…awake with a tummy ache!” he rubbed his own tummy in a very childish way. To make it even worse, it felt to Jamie like Bobby was singing directly to him because of where he was sitting. Jamie cringed repeatedly at how sissyish the whole performance was… it was like watching a petticoated train wreck!
As the music ended, the ladies erupted into more titters and applause. Jamie heard comments of “So precious!” “He looks so sweet in his dress!” and “Encore, Encore!” At Daphne’s prodding, the thoroughly emasculated teen performed one last dainty curtsey. Jamie felt his skin crawl in sympathetic embarrassment, and he saw Mrs. Green had recorded the whole thing on her phone!
Mrs. Green spoke with pride, “Wonderful Bobby! Just wonderful!” Then, she added for the group, “I’ll bet I heard that song fifty times this week as he practiced it with Daphne, but it turned out adorably!” Several of the ladies openly chuckled at that as Bobby just stood there looking like a bashful little child.
Although it remained hidden under his frilly apron, the unwelcome excitement in Jamie’s pants returned with a vengeance!
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Part 8
At that point, Jamie’s mother insisted he go stand with Bobby so that she could take more pictures. Both of them blushed brightly as she snapped photos of the boys in their coordinated outfits. Susan Padgett appreciated how sweet the “little couple” looked together, but she also began to imagine how much more adorable Jamie would look in a dress. Not for the first time this afternoon, she felt she had missed an opportunity.
“Well, that concludes today’s book club, ladies. I hope you enjoyed yourself” Mrs. Green announced. She added, Bobby and I look forward to hosting you again in a couple of weeks!”
One of the other ladies, Mrs. Abigail Thomas, asked in surprise, “Oh, is Bobby going to join us again next time?” Mrs. Thomas was the mother of another boy in the same class as Bobby and Jamie.
“Certainly,” Mrs. Green replied. “Because of all the problems he’s caused lately, Bobby will be joining us as a ‘junior hostess’ for another six months at the very least. The trouble he got into last time was just the tip of the iceberg!” She added, “Besides, I didn’t go to all this effort for just one day!” She smiled expectantly at her feminized teenager as she spoke. Bobby was crestfallen as he clasped his daintily gloved hands in front of him, but he managed to force a weak smile. He already knew he faced months of petticoating in his immediate future. “As of now, his petticoating sessions are generally limited to his time at home and at these book club meetings,” she noted, “and I also found a teacher who has accepted him into her girls’ ballet class, so he’ll start those lessons next week!” She added, “and of course I’ll need to take him shopping soon too so we can pick up some additional items for his wardrobe!”
Addressing Bobby directly, she asked cheerfully, “Won’t it be fun to pick out some more pretty things to wear, dear?”
“Yes Ma’am,” Bobby replied in a soft voice as his face continued to blaze.
Jamie thought Bobby looked incredibly dispirited as he just stood there meekly in his party dress. As Mrs. Green discussed her intentions so openly and matter-of-factly, Jamie was dumbfounded at the awfulness of Bobby’s plight. He also fretted even more about his own precarious situation.
Mrs. Green continued, “that’s the extent of his Petticoat Time… for now.” With a hint of warning in her voice, she continued, “Bobby is keenly aware, however, that things can change in a heartbeat if he starts to backslide or fails to show the proper enthusiasm. If I need to implement ‘Fulltime Petticoating’ to get the desired results, then so be it!”
“Proper enthusiasm?” Mrs. Thomas inquired, somewhat perplexed. “Do you mean to say that he is actually eager for his petticoats and dresses?”
Mrs. Green chuckled slightly, “Oh no, of course not… at least not yet anyway.” She added, “perhaps ‘motivated’ is a more accurate word.” She went on to explain, “proper petticoating involves clearly defined stages. With Bobby, as I alluded to earlier, we zipped right through the first two stages of Denial and then Defiance in just a few days.” With a satisfied smile, she added, “again, I was… adamant. Bobby quickly understood that fighting the process would only make things worse for him in the end!” Looking with satisfaction at her sissified son, she went on, “now Bobby is well into the Compliance stage. Although it’s obvious he still detests his petticoating, he now obeys promptly when his Petticoat Time starts! He’s dropped practically all traces of resistance or recalcitrance. Of course, I make sure to promptly address the occasional misstep or any lingering sign of willfulness! I’m happy to say that Bobby is rapidly learning the value of compliance and acquiescence!”
Mrs. Thomas and all the other ladies seemed amazed to hear how detailed Mrs. Green’s petticoating methods were, but Bobby’s mother was not yet done: “After a sustained period of strict and comprehensive petticoating, Bobby will eventually reach the Acceptance stage. In that stage, his aversion to the process will subside, and he will accept his sissification as part of his normal reality. There’s no doubt I will get him there… it's only a matter of time and effort!”
Mrs. Green paused for a moment, and then she continued, “Unfortunately, however, the Acceptance stage is as far as many petticoated boys ever get. Still, with enough persistence and close supervision, I am optimistic Bobby will at some point blossom into the Appreciation stage. This is the culmination of the ‘Petticoating Journey.’ At this point, he will come to treasure the structure and security his Petticoat Time provides him, and he will eagerly seek to expand it on his volition. He will crave it! He will long for the peace of mind and clarity he feels when he’s wearing his dresses. He will feel true gratitude for the entire experience. If I can successfully guide Bobby to the Appreciation stage, then perhaps we will have other decisions to make, but you get the general idea.”
“My goodness!” Mrs. Thomas exclaimed in admiration, “I had no idea!”
“The methods are tried and true… it’s just a matter of persevering and staying the course!” Mrs. Green replied confidently.
Hearing all this laid out in such detail, Jamie was aghast as he realized the full extent of what Bobby’s mother had planned for him and how far she was prepared to go. He shuddered at the prospect. How could Bobby just stand there and take it!?! He looked back over at Bobby, and he was struck by how timid Bobby looked. It seemed obvious that Bobby had already surrendered.
Next, he was rudely surprised when he heard his own mother make an announcement to the group. The look on her face made it clear she was absolutely enthralled with Mrs. Green’s zealous new approach to youth discipline! With barely contained enthusiasm, she blurted out, “Jamie will also be joining us again next time!” He felt his own face heat up in embarrassment as she added ominously, “and if he’s not careful, he may find himself in a frock too!” Jamie was horrified now, and he fidgeted nervously in his own delicate lace gloves and feminine apron. His heart thumped faster, and the unwanted pressure in his pants worsened!
Mrs. Thomas spoke again, “Well you’ve certainly convinced me! I’m going to bring my son Jason with me to our next meeting too. It’s no secret that Jason could stand to improve his behavior, and it might be helpful for him to see what could happen if he doesn’t shape up!” she said. Then, with a gesture toward Bobby, she said with admiration, “I applaud the way you’ve brought this one to heel!”
Jamie’s spirits sank as he realized the danger that loomed before him. Right then and there, he concluded that he had to remain on his absolute best behavior to avoid a fate like Bobby’s. Going forward, he resolved to avoid even the tiniest hint of trouble. He wouldn’t give his mother any reason to pursue a similar path!
Susan Padgett admired her smartly dressed teenager in his girlish apron and gloves, and she reached a slightly different conclusion. Come hell or high water, Jamie would most definitely be wearing his own adorable dress at the next book club! If he somehow managed to avoid any misbehavior in the coming days, then she’d just have to invent an excuse. She’d already begun to rationalize that it wasn’t fair for Bobby to be punished alone while Jamie got off scot-free. After all, he had been a willing accomplice in their escapades last time even if he hadn’t initiated them.
In any event, it was decided. Diane Green’s last comments had sealed the deal. Susan Padgett thought back to the scolding she had given Jamie a couple of weeks ago and giggled. Bobby Green had indeed jumped off a figurative “bridge” of sorts, and now she would ensure Jamie jumped right after him! By the time the week was over, Jamie would follow his sissified classmate into childishly cute dresses and petticoats of his very own! Very soon, Jamie Padgett would embark on his own petticoating journey.
As she studied her embarrassed 13-year-old, she smiled as she saw the trace of Bobby’s pink lip gloss still lingering on Jamie’s cheek. It made her think that a dainty pink party dress would be the right place to start! And perhaps some lovely tights as well! She quickly became enamored with that idea, and she found herself eager to start shopping! She also noted with satisfaction that Jamie’s hair was quite a bit longer than Bobby’s. That opened up so many delightful possibilities! She would need some help, of course, but now she had no doubt that Diane, Daphne and the other book club members would be eager to assist with another “petticoating project!”
Meanwhile, Jamie continued to blush and stew. He was oblivious to the fact that his future, like Bobby’s, was already set. Jamie was so consumed in his own thoughts that he never even heard the question his mother quietly asked Mrs. Green, “Diane, do you suppose I could get the name of that ballet teacher?”
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Delightful story, can't wait to see how Jamie reacts to being dressed in a pretty pink dress and taken to the book club to join Bobby.
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I can see Jaime not being fast enough to show up for dinner as a reason to get punished. I am thoroughly enjoying this story. It just keeps getting better
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Jason Thomas will be boy number 3. He will join Jamie and Bobby in serving the ladies at the "Book Club."
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I love this story. As exciting for the reader as JOSH but such a different plot.
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Another wonderful story sissyboy1212! I hope you’ll be inspired to continue it, I’ve been checking daily hoping for an update on Jamie’s progress!!
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Thanks! I’ve got an epilogue drafted, but it’s not quite there yet. There may be another part before the epilogue… still deciding.
I appreciate the encouragement :)
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I decided to expand and rework the original ending I had written, so there will be a small number of additional chapters before I post the epilogue. Hope you enjoy!
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Part 9
Two weeks later, the ladies of the book club reconvened. Just as before, they all gathered in the great room of Mrs. Green’s spacious house and took seats around the little white tables. This time, however, there was a noticeable sense of anticipation in the air as the meeting began.
“Welcome back ladies,” Diane Green began with a chuckle, “and I also want to welcome another special young guest as well.” Gesturing toward Mrs. Thomas, she said, “Abigail has brought along her son Jason to be with us today.”
Much like Jamie Padgett two weeks earlier, Jason Thomas sat uncomfortably next to his mother and reddened slightly to be made the center of attention. At first, he had been annoyed to be dragged to such a boring and stuffy affair, but now he was nervous.
“Be sure to pay attention, Jason,” Mrs. Green continued, “I’m certain you’ll find our meeting… educational.” Several of the ladies tittered at that remark, and Jason shifted uneasily in his chair.
Turning back to the group, Mrs. Green went on, “As I think most of you know by now, Bobby and Jamie will join us again momentarily to help serve the refreshments. They’ve certainly had an eventful couple of weeks, and I’m sure Susan is eager to show you Jamie’s… new look.” Mrs. Green shot a brief glance back to Jason, and then she continued, “so without any further ado, let’s get started with our meeting, shall we?”
Just outside the door, Daphne spoke to Bobby and Jamie with a little giggle, “OK… boys… it’s showtime!” She put a teasing emphasis on the word ‘boys’ to emphasize their current plight as she gave Bobby a playful little nudge toward the door.
Jamie winced as he felt his mother’s hand touch his shoulder, and she began to guide him into the great room as well.
“Let’s go, dear,” Susan Padgett directed her discomfited teen. She added teasingly, “I know you’re excited to show off your pretty new outfit!”
Both boys blushed brightly as they were escorted toward the door.
Jamie’s emotions were a whirl. “It wasn’t fair!” he miserably thought to himself. He had been extra good ever since that last book club meeting! He had done all his homework and chores without being told. He had stayed out of trouble and not complained at all when it was his bedtime. From his standpoint, he had practically been an angel!
Then, last Friday afternoon, it was as if none of that mattered at all. Jamie had come from school to find that Mrs. Green, Daphne and Bobby were all there waiting along with his mother. Jamie had been dismayed to see that a very red-faced Bobby was already wearing a darling lavender A-line dress covered in white polka dots. It seemed to have ruffles everywhere. His petticoated friend also wore a cute matching pair of lavender Mary Janes on his feet!
His mother had then informed him that the grades on his monthly progress report were not up to snuff, and besides she had decided that it just wasn’t fair that Bobby was being punished alone for something they both took part in. Jamie was almost numb in shock as she announced that he would begin a regimen of petticoat discipline as well, starting immediately! “I’ve concluded that some quality time spent in skirts and dresses will do you a world of good, dear. It’s all decided!” Caught off guard, Jamie had hardly mustered any meaningful resistance at all to his mother’s intentions while Bobby just watched meekly. Mere minutes later, with a slightly sore bottom and tear-streaked eyes, Jamie had been dismayed to find himself confined in the frilly blue dress and black Mary Janes that Bobby had worn at the last book club! They had even made sure to remember the adorable white anklet socks with the lace ruffles!
Outnumbered and overwhelmed with the sudden change in his situation, he had stood powerlessly as Daphne affixed the same precious hairbow in his hair that he had pinned into Bobby’s the week before. All the while, Bobby had just waited there with a defeated expression on his face as Jamie was quickly and methodically put into a dress for the first time!
With Jamie’s eyes continuing to water, his mother had ushered him over to the large mirror in the foyer. Dejectedly, he had taken in his sissified appearance for the first time. “There now,” his mother had said enthusiastically, “you’re as pretty as a picture!” Jamie had stared glumly at his image as she continued, “Mrs. Green was so nice to let you borrow Bobby’s dress for today, but you’ll have your own nice things by tomorrow!”
The following days had been an awful blur of one sissified humiliation after another as his petticoating education began in earnest. Day after day of dresses and dolls and curtsies and a seemingly endless parade of girlish clothing and activities. It all seemed to pale in comparison, however, to what he knew awaited him at the book club meeting now. Now, his heart fluttered as he and Bobby entered the great room.
Bobby walked in first, and the ladies began to murmur in approval as they took in the adorable outfit the beet-red boy wore. Bobby was smartly buttoned into a precious tulle party dress and looked ready for a pageant! His dress was a lovely pastel yellow color with layers upon layers of dreamy tulle frills. The beautiful dress sported a dainty sweetheart neckline and oversized puff sleeves that ballooned prominently over his narrow shoulders. Whimsical layers of gauzy tulle with bits of glitter adorned the bodice, and the tutu-style creation gathered nicely at the petticoated boy’s waist. An elaborate yellow satin bow accentuated the waistline above his extremely poofy knee-length skirt. His expansive skirt boasted even more layers of bouncy pastel tulle that swished and swayed delightfully with the assistance of a very full petticoat underneath.
Bobby’s legs were sweetly encased in a darling pair of patterned white tights. The childish tights sported a delicately girlish floral lace pattern that was just gorgeous in contrast with his frothy tulle skirt. Strapped on his feet were a glittery pair of pale yellow ballet-style flats with fussy little ankle straps encircling his ankles and sparkly yellow bows on the toes. Pinned in his curly blond hair was the cutest hair clip with an enchanting yellow butterfly decoration. The delicate butterfly’s wings had wonderful metallic accents that caught the light and glimmered just adorably. The entire outfit sparkled and bounced with such captivating girlishness!
As several of the ladies practically gushed over Bobby’s outfit, Mrs. Green said, “and now here’s our newest junior hostess!”
Grimacing, but having no choice, Jamie reluctantly followed his classmate into the great room. His face burned and his heart pounded as he was paraded before all the ladies. Their murmuring became notably louder, and there were also more than a few perplexed looks. Susan Padgett had a very satisfied smile on her face as she ushered her petticoated teen into the room.
It was immediately obvious that Jamie was outfitted in the exact same style of dress as Bobby. Instead of yellow tulle, however, Jamie’s frock was a vision in pastel pink! As Jamie minced nervously into the room under his mother’s watchful eye, the noisy rustling of his sissified pink party dress nearly drove him to distraction. On full display now, Jamie knew that every eye was on him as he followed his classmate to the front of the room. The layers of fluttery pink tulle tickled him ceaselessly, and he was very conscious of how clingy his patterned tights felt underneath his elaborate skirt and petticoat. Every movement he made triggered a cascade of tulle swishes and rustles. Like Bobby, he wore his darling “tea party gloves” from the last meeting with their silky white ribbons securely tied around his wrists. Humiliated, Jamie stood next to Bobby at the front of the room as the assembled group inspected them thoroughly.
Indeed, the petticoated boys’ delightful dresses were identical except for the colors. Bobby looked so sweet in his pastel yellow, and next to him Jamie stood helplessly in his darling ballet pink. Of course, there was one other glaringly obvious difference in their appearances which had been the source of all the confused looks.
As Jamie cringed brightly, Jamie’s mother spoke for the first time. Smiling, she said, “Jamie’s look is obviously not quite finished, but after talking it over with Diane, we thought it would be appropriate to let you all see the final reveal!” As she spoke, she steered Jamie to a chair in front of her and gestured for him to take a seat. She let her hands rest purposefully on her sissified son’s shoulders and continued expectantly, “this should only take a few minutes!”
With his face still burning, Jamie sat down gingerly and fretted in awful anticipation. He desperately tried to gather his voluminous skirts underneath him, but he quickly realized it was hopeless. The swishing mounds of frothy tulle continued to pop up incessantly. As Jamie wrestled futilely with his skirts, the newly-petticoated teen finally caught sight of his other classmate Jason gawking at him as a full witness to his sissified humiliation. Jamie locked eyes with Jason, and that only served to deepen the feelings of helplessness and embarrassment that consumed him now. He was a teenage boy, and it crushed him to know that he was exposed this way as the most girly-girl sissy he could imagine! Underneath the dancing layers of pink tulle and his gaily patterned lace tights, Jamie was horrified to feel an unwanted tightening in his nylon panties.
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I'm having a little trouble figuring out the transition to the next part, but I expect it will be ready in the next few days.
I just like for it to be "right" before posting. Thanks for the positive vibes ;)
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Jaime getting punished again for his actions, weeks later, is wrong, but I love it.
Take your time, get everything the way you like it
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Part 10
Diane Green sensed it was time for her to take charge. Jamie’s mother was certainly enthusiastic, but she still had some things to learn about the finer points of petticoating. Interjecting now, Diane spoke again as she gestured toward Jamie, “Ah yes,” she began, “it’s obvious many of you are wondering about these!”
All attention was now squarely focused on Jamie, or more specifically his hair. As the flustered teen blushed fiercely and felt a trickle of sweat form under his bra strap, all the ladies inspected the mass of pink curlers neatly rolled into his longish brown hair! Jamie was mortified to be on such full display, and he was very conscious of the unfamiliar weight of all the feminine curlers pinned so meticulously on his head. Reflexively, he fidgeted with the tulle layers of his prissy skirts which just created more swishing.
Diane said with a smile, “A petticoated boy’s first time in curlers is a wonderful milestone in his Petticoating Journey, and Jamie is so lucky to experience that right off the bat!” She looked over at her own feminized son a little wistfully, “Soon enough I’ll have Bobby’s hair grown out long enough to join him, but today is Jamie’s moment to shine!” Bobby winced to be reminded of what lay in his own future. Diane continued, “I suggested to Susan that it might make the occasion even more memorable if we unveiled his new hairdo with an audience, and I felt sure you would all appreciate the opportunity to watch!”
“Quite right,” one of the other ladies chimed in cheerfully. There were several nods and pleased looks from the other ladies. The overwhelming sense in the room seemed to be that Jamie had gotten off far too lightly last time for his part in all the shenanigans, and that those chickens had finally come home to roost. Sitting skittishly next to his mother, Jason Thomas seemed to be the lone exception to this feeling as his eyes bulged in near disbelief.
Still standing over her petticoated son, Jamie’s mother beamed as she spoke again, “Thank you again Diane, I must admit I am quite eager to see the results!” Then she turned to Daphne and said, “and thank you Daphne for volunteering to do the honors. For those that don’t know, she is quite gifted with hair!”
Daphne nodded in appreciation and said, “Of course, Mrs. Padgett! Shall we get started?”
“By all means,” Jamie’s mother replied enthusiastically.
Jamie was as skittish as a cat as Daphne stepped toward him with a pink can of hairspray. “Close your eyes, sweetheart!” she directed. Jamie meekly obeyed as Daphne sprayed a generous coat of Extra Hold hairspray on his pink curlers. As the mist dissipated, Daphne announced, “we rolled his hair with the heated curlers a couple of hours ago and applied a rather strong setting spray, so his curls have had ample time to dry and form!” Cringing, Jamie remembered every unsettling sensation of being put into these curlers earlier, and now he had a whole audience watching to see his curls revealed! He wished he could disappear into the floor. The teenaged boy felt so sissified and defeated as he sat in his pretty pink party dress before the entire book club to get his hair styled. He shuddered every time he saw Jason staring at him in astonishment. Glumly, he brushed his skirts again with his daintily gloved hands.
Daphne began methodically removing Jamie’s pink curlers. She had Bobby stand right next to his seated classmate and hold a pink plastic bin for her. As she took out the curlers one by one, she dropped them into the bin. In such proximity, the boys constantly brushed their springy dresses against each other while Daphne worked. Every time Daphne changed position, she would have Bobby adjust as well, but she always kept him immediately next to Jamie. As a result, the two boys’ gauzy yellow and pink tulle skirts swished and flittered together to create a charming sight as Bobby minced around to collect the curlers! Jamie’s pink skirt was in near constant contact with Bobby’s pretty tights, and Bobby’s yellow skirt continually tickled Jamie’s arms and spilled onto his lap. It was a delightfully frou-frou show for everyone to watch! As Daphne took out each curler, she would fussily arrange the new curl with her nimble fingers. Jamie’s skin crawled as everyone in the room watched his girlish hairstyle appear. The pressure in his panties was mounting!
Meanwhile, Jamie’s mother was thrilled as she watched her son’s lovely new hairdo take shape. She had known in her heart that his longer hair would be adorable with the right styling, and now she was seeing the proof of it before her eyes! After the last few days, she was absolutely certain that petticoating Jamie had been the right decision.
As Daphne was finishing, several of the ladies began making comments of approval such as “How cute!” and “So precious!” After she removed the final curler, she teased Jamie’s hair a bit more and then instructed her petticoated brother, “Bobby, hand me Jamie’s hair clip please.”
Jamie watched helplessly as Bobby took a hair clip from the plastic bin and handed it to his big sister. It was a dainty little butterfly clip just like Bobby’s, except his clip was a delicate shimmery pink to match his dress. Daphne carefully pinned it in place and had him stand up beside Bobby. There was a cacophony of approving comments when all the ladies saw his finished hairstyle. Now, Jamie’s hair was a beautifully feminine vision of cascading brunette curls!
“Beautiful!” Jamie’s mother exclaimed. “You look just like a little princess Jamie!”
“Take a look, Jamie,” Daphne said as she held up a hand mirror. Jamie was crushed to see the toddlerish hairstyle he now wore! He hesitantly touched one of his fancy new curls with his delicately gloved hand and immediately saw how playfully springy it was! His pink butterfly hairclip looked just darling nestled in the dainty curls, and his sissified look was complete.
Jamie’s mother gushed and prodded her son, “don’t you feel so pretty with your new curls, dear?” The look in her eye made clear the type of answer she expected, “If we were at a wedding, you would make a lovely bridesmaid or even a cute flower girl!”
“Yes ma’am,” Jamie practically croaked. “I… I love them,” he managed to spit out. It pained him immensely to know how girlish and feminine he was now.
Daphne couldn’t resist adding with a giggle, “Don’t you worry Bobby! Your first time in curlers is coming soon!”
As the petticoated pair stood self-consciously in their fussy dresses and frills, the ladies spontaneously broke into a smattering of light applause. It was obvious that the prevailing mood of the room was appreciation at seeing these two misbehaving teens put emphatically in their place! Many of the book club ladies had their phones out taking pictures, and Jamie agonized over where those pictures might end up!
Beaming, Daphne brought their hands together so the two sissies could hold hands for the photos. Jamie and Bobby looked positively adorable in their coordinated pink and yellow ensembles! It was apparent now that they were wearing lip gloss again, and it was a deeper shade of pink than at the last meeting. In fact, if their faces hadn’t been so red, the rosy blush on their cheeks would have been obvious too. From their sparkly ballet flats and angelic patterned tights all the way up to their whimsical butterfly hairclips, it was apparent that Diane Green’s “total immersion” approach to petticoating was in full effect!
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Can’t wait to see Jason get his soon
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PART 11
One of the ladies remarked admiringly, “Oh Diane, our junior hostesses both look so lovely! You, Susan and of course Daphne have done a fantastic job on the details!” She surveyed the sissified boys and added, “I’m amazed at how you’ve just scrubbed out all the bratty boyishness in these two and turned them into such darling little sugarplums!”
Jamie and Bobby were crushed to know it was all true. As Jamie felt the unfamiliar weight of his springy little girl curls and the rustling of his fussy dress, his spirits sank at the prospect of the months of petticoating in his future.
As if on cue, Diane Green spoke again, “Thank you, and I assure you that none of it was an accident. As I’ve discussed with Susan over the last week, I believe that petticoat discipline should be in-depth and unfailingly consistent!” As she admired Jamie’s new hairdo, she said, “I’m sure that little Jamie will not soon forget the thrilling experience of being put into his girly-girl curls with all of you today!” With a somewhat pleased look, she said, “In fact, thanks to Susan’s enthusiastic adoption of proper petticoating principles, I think we’ve gotten Jamie here to the ‘Compliance’ stage even faster than I did Bobby!” She added, “it’s all about making a lasting impression!”
Susan added, “Thank you, Diane. You and Daphne have been such a help, and Jamie’s curls are just scrumptious!” Then she added, “I love the way they just flit and tumble on him so adorably! I’m already thinking that I may take him to get a perm!”
“A perm?” Jamie thought with horror! He felt another electric pulse in his panties as his heart sped up!
Diane smiled at that thought. That would indeed be a nice step. After a moment, she resumed speaking, “Petticoating should be deliberate and structured… it’s not just about putting a boy in a dress!” She went on, “No, it’s about creating a set of conditions that will make a memorable and lasting impact! That’s how you achieve real behavior change!”
“Take Bobby here,” she offered. “As I explained last time, Bobby has so far avoided Fulltime Petticoating through his newfound obedience, but his Petticoating Time is still highly organized.” She pointed to the side of the great room, “Do you see that digital clock on the wall?” Everyone turned to see a large digital clock hanging near the entrance. “I have several of those around the house, and they are all synchronized and linked to my phone. Every day when Bobby comes in from school, I set a timer for thirty minutes, and all the clocks begin to count down together.”
She smiled, “Bobby is permitted to do anything he chooses during that free time. He can watch TV, or have a snack, or even play his video games…I really don’t worry about him misbehaving at all. He knows that when the timer is up and that little chime sounds, it’s the start of his Petticoat Time!” She added with a little amusement, “Oh you should see the anticipation that builds in him as those minutes dwindle down… especially on Fridays when the whole weekend awaits!” With satisfaction, she went on, “That’s an example of how you make a real impression!”
Shifting uneasily in his frilly dress, Jamie grimaced as Bobby’s mother talked. His mother was already applying the same routine to him, and he knew exactly how dreadful it felt to watch his time slip away. His stomach turned into an ice ball every afternoon when that little chime went off! In his darker moments, he almost thought it would be better not to have the free time at all!
Abigail Thomas seemed to gain interest in the mechanics of this process, and she asked “so he goes and gets dressed when the time is up? Is that how it works?” Sitting next to her, Jason immediately took notice of his mother’s curiosity.
“Oh, heavens no,” Mrs. Green replied, “as I said it’s much more structured and deliberate than that!” She explained, “Bobby knows he is to be waiting in my bedroom before that chime goes off! I keep all his lovely petticoating clothes there in my extra closet. I usually come in a minute or two later so we can get started. He’s only kept me waiting once, and I think he learned his lesson quickly as we haven’t had a recurrence!”
Diane smiled maternally at Bobby and said, “We’ve developed a delightful little routine, haven’t we honey?” Without waiting for him to respond, she said cheerfully, “Bobby, let’s show the ladies how we start off!”
Bobby shifted his feet uneasily, and his prettily gloved hands fidgeted nervously. Enveloped in all the flittering layers of his adorable yellow tulle dress, he looked so sweet as his face reddened again.
Playfully, Bobby’s mother asked him, “what time is it sweetie?”
After a moment, he replied in a hesitant voice as if reading from a script, “it’s my Petticoating Time Mommy.”
Diane smiled at her embarrassed child and continued, “and what’s the magic word, Bobby?”
The sissified thirteen-year-old took a quick breath and then asked with a miserable look on his face, “Please… Please can I get dressed in my pretty things now?”
“Of course, dear,” his mother beamed while Bobby looked at the floor in defeat. Then she spoke again to the group, “I think it helps his mindset to verbalize this way, and it’s become a wonderful time for mother-son bonding!” Diane continued, “after he asks to get dressed, I select his clothing, and then I dress him, often with Daphne’s help.” She smiled at Bobby, “it’s important that Bobby is PUT into dresses and petticoats… he’s not allowed to dress himself.”
Then, Diane seemed to catch herself. She shook her head in a charming way as if to chide herself, and then she said almost apologetically, “I’m so sorry that I’m blathering on. I’m sure I’ve bored you to death!”
“Oh no, Diane, please continue!” Abigail Thomas replied at once. Jason Thomas warily noted his mother’s continued interest in this conversation.
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I have a feeling Jason isn’t going to be leaving the meeting the way he arrived
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Part 12
Gratified, Diane surveyed the room and realized that all the ladies still seemed intently interested in what she had to say. Jamie and Bobby, standing sweetly together in their fussy dresses, looked anguished as their predicaments were described so publicly. Jamie was beside himself as all the details of his rapid sissification were exposed this way. Meanwhile, his classmate Jason sat with a funny look of bemusement on his face as if this were some elaborate hoax.
“Thank you for indulging me, Abigail,” Diane Green responded with a smile, “I do think that the distinction is crucial!” She continued, “when a boy is PUT into his girlish things, it reinforces that his petticoating is a discipline with a clear GOAL… not a game!” She added, “this makes clear that he is not in control of the situation and thus helps stifle his willful tendencies!”
She went on, “it also ensures that the wayward boy is properly dressed down to the very last detail. I’ll give you an example of why this is critical. You can’t see it right now, but Bobby is wearing the cutest little bra and panty set under his dress and tights!” She chuckled as an aside, “In fact, Jamie here is also wearing an identical set! I happen to know since I bought them both!” She continued, “The point is that absent the right supervision, these boys might ‘forget’ such things!”
Jamie and Bobby squirmed uncomfortably to be reminded that they were sissified all the way down to their underwear, and several of the ladies chuckled. Jason Thomas could not believe what he was hearing and seeing. His classmates were even wearing bras and panties!
“I also maintain,” she said, “that petticoated boys should be put into the most elaborate and ultra-girly outfits possible… preferably with lots of buttons, buckles, ribbons, ties and so forth to help constrain any lingering traces of defiance. As far as I’m concerned, the more layers, frills and accessories the better! Like I’ve said before, the goal is to ensure nothing masculine remains so that the petticoating is free to work its magic!” She finished her thought, “such close supervision has a practical aspect as well since it can become very difficult for a boy to get into… or out of… such fancy trappings without help.” She chuckled and glanced at Jamie’s mother as she added, “In fact, Susan and I have just decided to begin corset training for these two, so that last part will apply even more when they are securely laced into their stiffly boned corsets!”
Hearing this, Jamie and Bobby looked completely defeated and emasculated. This was the first mention they had heard about their impending corset training! Jamie was horrified that the pressure in his panties seemed to grow more intense at the awful thought of being laced tightly into a corset!
As Diane Green finished, the ladies murmured in awe and admiration at the level of planning and commitment she put into her petticoating philosophy. Susan Padgett nodded in approval; she was thrilled that she had put Jamie on the same path as Bobby.
Diane concluded with a grin, “and now that Jamie here has begun his own Journey, these two will be able to have more lovely Petticoat Playdates… heavily supervised of course!”
“Oh yes,” Jamie’s mother said enthusiastically, “In fact, we had a very sweet playdate yesterday and you should have seen the two of them! After we got them nicely dressed, they did all their homework together and later worked on their deportment. Then, as a treat, Daphne taught them how to do manicures, and the boys got to paint each other’s nails! So cute! It was such a lovely time!” Both boys grimaced at that memory.
Diane had a satisfied look on her face as she eyed Bobby’s newly petticoated friend. It was such a treat to be able to mentor Susan in the benefits of petticoating, and she thought Jamie was coming along nicely in his new journey. Jamie’s girlish curls were just precious, and Diane looked forward to Bobby getting his own in the very near future.
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I love this story! thank you so much!
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Part 13
Then, however, Diane’s keen eye noticed something amiss, “Speaking of supervision, Susan, it appears that Jamie has allowed the seams on those adorable tights to get all crooked.”
“It seems you’re right, Diane” Susan Padgett agreed as she scrutinized Jamie’s gauzy floral stockings, “attention to detail is so important!” With a little frown, she instructed her petticoated teen, “come here at once so I can fix them for you, Jamie!”
“Oh, don’t trouble yourself, Susan,” Diane replied, “I’ll have Bobby do it.” Addressing her own son, she directed, “Bobby, please help Jamie with his tights, dear… those unsightly seams just will not do!”
Cringing to be singled out again, Jamie tried to look down and check his seams, but it was useless. His buoyant tulle skirt made it impossible for him to see them properly. Bobby, meanwhile, was chagrined at the new task he had been assigned. Both feminized boys looked pitiful as all the ladies watched expectantly.
Unprompted, Daphne gleefully stepped in to assist her little brother and retrieved the little stool from the corner. She placed it immediately next to Jamie, and then she prodded Bobby to have a seat. Jamie’s heart pounded and his mouth grew dry as he realized what was going to happen. While Jamie stood in his pretty frock facing the ladies of the book club and his classmate Jason, Bobby sat down next to him and began delicately tugging on his clingy tights! Jamie was overcome with a feeling of utter helplessness as Bobby began to nervously pluck and pinch on the stretchy material. Under Daphne’s painstaking guidance, Bobby repeatedly tugged and straightened the seams of Jamie’s delicately patterned stockings. Each little tug seemed to create electric tingles that pulsed into Jamie’s panties. It only got worse as Bobby unavoidably rustled the layers of Jamie’s lovely pink tulle petticoat over and over as he ensured everything was just so. When Bobby finally got the left leg perfectly straight, Jamie let out a quick breath and trembled slightly.
Bobby continued to pull and straighten the seams on the right leg now, and each little adjustment created a new jolt of friction on Jamie’s skin that made him increasingly lightheaded. Incredibly dismayed, Jamie tried to control himself and took a couple of short, shallow breaths. As Bobby gave one last little yank to get the seams exactly right, Jamie felt his clingy tights suddenly shift again across the front of his silky panties. Involuntarily, Jamie shuddered. It was all too much! He felt a telltale tingling pulse under his tulle petticoat, and then, the inevitable happened. Humiliated, Jamie turned an even deeper shade of crimson as he exploded into his panties! Reflexively, he let out a little gasp and put his hand on Bobby’s shoulder to steady himself. He was horrified as a creamy mess quickly filled his lacy panties.
Remarkably, most of the ladies didn’t seem to realize what had just happened, but Diane Green had a knowing look of amusement in her eyes. She understood the situation precisely. In fact, she knew it was hardly unusual for newly petticoated teenagers to become over-stimulated by the flood of unfamiliar sensations and emotions. As a boy gradually lost more and more control of his destiny and became rapidly immersed in girlishness, he also tended to grow more skittish and high-strung. Finding himself progressively enveloped in dresses, skirts and frills, it wasn’t surprising that the slightest thing might send a boy into a panic and over the edge! That was why she had insisted from the start that first Bobby and now Jamie always wear scented panty liners in their panties just in case! The added protection just made little sissy accidents much easier to handle! With satisfaction, she also knew that this turn of events would just make the day even more unforgettable for little Jamie and further enhance the effectiveness of his petticoating! The memory of losing control in such a public way would definitely leave a lasting mark!
Meanwhile, Jamie was disconsolate as the reality set in, and his shame deepened. The warm wetness under his tulle skirts and panties was inescapable. He felt nightmarishly exposed and vulnerable in his pretty pink party dress!
Then, to make things worse, Daphne leaned over and whispered teasingly in his ear, “I think someone just made a sticky-icky in his panty-wanties!” She added softly, “Poor thing, I guess the excitement was just too much for you!”
Jamie was crestfallen as the pounding of his heart began to subside. In only a few days, he had been totally sissified just like Bobby. Every slight movement of his head seemed to make his new girly-girl curls bounce in the most feminine way. The floral white tights encasing his legs seemed to tingle with each tiny movement, and the swishing and fluttering of his tulle skirts and petticoat were maddening. The dainty tulle accents on his girlish puff sleeves tickled his slender arms ceaselessly. His sparkly pink slippers felt so delicate and unfamiliar on his feet. His palms were perspiring in his adorable tea party gloves which were tied so gaily around his wrists with their darling ribbon ties. He could still taste the strawberry flavor of his shiny pink lip gloss. Worst of all, he had just made a humiliating mess in his panties, and it was only a matter of time before his mother found out!
He was a teenage boy, and yet here he was completely cocooned in lace, tulle, ribbons and ruffles for all these ladies to see. It seemed that every moment brought him the terrible promise of even deeper levels of girlishness. His heart fluttered, and his throat grew dry. The awful weight of a long and involved Petticoating Journey hung over the feminized boy like a cloud. Looking up, his humiliation intensified even more when he saw his classmate Jason staring intently at him again.
Diane Green sighed and said, “Well I’ve gone on about petticoating more than long enough, ladies. Let’s move on to our book discussion while Daphne gets our adorable junior hostesses ready with the snacks, and perhaps she might also need to help Jamie… freshen up!” She added that last part with a barely suppressed giggle as she scrutinized the blushing sissy. Then, in a rather obvious whisper, she told Daphne, “The panty liners are in the powder room!”
Susan Padgett heard that last instruction and fixed her gaze intently back on her embarrassed son with new interest.
At Daphne’s prompting, both petticoated teens dropped into charming little curtseys. Jamie’s was understandably wobbly, but Bobby’s was nearly flawless. Completely chagrined, the petticoated boys meekly prepared to follow Daphne. Jamie’s spirits deflated as Mrs. Green’s last comment sank in. Clearly, she already knew about the mess in his lace-trimmed panties!
As if on cue, Jamie saw Mrs. Thomas turn to Jason with a smirk on her face. Teasingly, she asked her son, “Well do you believe me now, dear?”
Jason didn’t respond, but he instead blushed slightly and locked his gaze back on his emasculated classmates.
Jamie felt that Jason was scrutinizing him especially. There was nothing he could do to prevent every girlish detail of his petticoating from being totally exposed. The gooey mess in his panties was starting to get sticky, and he fought the urge to cry. In that moment, the petticoated sissy glumly surrendered to his fate. He knew that he would never forget what had just happened. Jamie also knew that he was now, unquestionably, a Compliant Petticoated Boy! Without even realizing it, he girlishly swished his pretty tulle skirt again.
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EPILOGUE: Jason’s Journey
An hour earlier, Jason Thomas had been nervous and out of sorts. When his mother first told him she was dragging him along to her book club meeting, he had groaned and grumbled. Why did he have to go to that thing?
Still, his mother was insistent that he dress smartly for the occasion, so soon he found himself wearing a somewhat juvenile outfit with lemon yellow trousers, a white dress shirt with little black polka dots, and a cute yellow bowtie. To top it off, she had also put him in some darling yellow suspenders and a lovely pair of white suede shoes. She had gotten this outfit for him to wear at a cousin’s wedding a couple of years ago, and he was embarrassed that it still fit. He had been rather surly about wearing it, but his mother left him no choice.
In the car on the way to the book club, however, his mood had shifted. His mother had mentioned that Mrs. Green had found a way to improve Bobby’s behavior, and that he ought to pay close attention himself. Then, she said that his friend Jamie was supposed to be there as well. But the kicker was when she used the term “petticoating.” He had never heard of that, but then she had explained what it was, and he had done a double take.
“You’ve gotta be joking,” he had said a little rudely.
“Oh, it’s no joke, dear,” she had replied confidently, “and just so you know Bobby’s mother even said that I could borrow some of his things for you if I wanted!”
Jason hadn’t said anything else after that, although he halfway believed his mother was pulling his leg. It just seemed too crazy. Still, he was wary now, and his mind started to race.
Then, while he was seated in Mrs. Green’s great room next to his mother, he had become a believer. When he had seen his classmates nervously mince into the great room under Daphne Green’s close supervision, he could not believe his eyes. As all the ladies tittered and made little comments, Jason’s jaw had literally dropped. It was all true.
Bobby and Jamie had both blushed brightly as they were paraded out in front of the ladies. Jason was dumbfounded to see his classmates dressed just like a pair of dainty little girls! He was practically speechless to see them transformed into such total sissies!
Despite himself, Jason was transfixed as he ogled his helplessly petticoated friends. The sight of Jamie being put into his little girl curls in front of all those ladies was almost inconceivable, yet he had witnessed it firsthand! Then, the whole spectacle of Bobby daintily adjusting Jamie’s tights had just been surreal. At one point, Jamie had been so panicky that it looked like he would faint! When he saw the two of them curtsey at the end, Jason was absolutely flabbergasted. Incredibly, his classmates just seemed to accept their feminized situations without any resistance at all!
That was when his mother had triumphantly looked his way and asked, “Do you believe me now, dear?”
As Jason began to grasp the extent of his classmates’ sissified predicament, he didn’t trust himself to respond. He felt his heart beginning to beat faster. He locked his gaze on Jamie especially as he scrutinized that incredibly girlish party dress. His red-faced classmate looked as though he was engulfed in a gauzy pink cloud of tulle and ruffles! Now, Jason cringed himself. He realized that he had to keep his wits about him. This situation was nuts! All the ladies seemed to smile at him knowingly, as if they already knew where this was headed.
As Daphne began to lead Jamie and Bobby away to prepare the refreshments, Mrs. Green seemed to remember that Jason was still in the room. She turned her attention to him and studied him for a moment. Jason shifted nervously in his seat, and he unconsciously fiddled with his suspenders as he felt her penetrating gaze. Then, with a twinkle in her eye, she suggested dryly, “Perhaps Jason would like to help Jamie and Bobby serve the refreshments today?”
His mother didn’t hesitate. “That’s an excellent idea, Diane,” Mrs. Thomas replied at once, “He’d love to!”
Jason’s pulse accelerated at this. Did she actually mean for him to join his utterly feminized friends? He decided to take a chance and push back on his mother. “No way,” he said sullenly, “I don’t want to do that.” This whole scene just seemed crazy to him!
Hearing Jason’s defiant response, Daphne and her two sissified charges stopped in their tracks. Jamie and Bobby both reacted in disbelief! They had already abandoned any semblance of resistance to their Petticoating, and the very idea of disobedience seemed to shock them now. Didn’t Jason know he was playing with fire? The tension in the room grew thick as everyone turned their attention to this unfolding drama.
Obviously displeased, his mother replied sharply, “Oh yes you will young man!” Then she spoke to Daphne, “Daphne dear, just show him what he needs to do.” She shot him another warning glance and said, “don’t test me!” Then, she firmly nudged her recalcitrant son forward out of his seat.
Jason blanched! Had he had gone too far? He could tell his mother was getting really annoyed now.
Then Daphne spoke up, “Of course! Let me get that darling little apron that Jamie wore last time… I bet Jason will look absolutely adorable in it with his cute yellow slacks!” Then she added teasingly, “unless, of course, he’d rather borrow one of Bobby’s dresses!”
“Apron?” Jason thought. He felt his face heat up even more. He gulped, and there was a long silence as Daphne’s taunt hung in the air. It was obvious to everyone in the room that Jason had quickly ventured onto very thin ice. Jason looked again at his totally emasculated classmates in their flouncy tulle dresses. They looked absolutely mortified and defeated. Jamie and Bobby stared back at him powerlessly, and he remembered the way they had performed such precious curtseys a few moments earlier. Then, in an unexpected show of obstinance, Jason blurted out, “I’m not wearing an apron or a dress, and you can’t make me!”
Everyone in the room seemed to hold their collective breath at his outburst. After a long pause, Jason’s mother replied icily, “We’ll just see about that!”
Then, Jason’s mother spoke purposefully to Mrs. Green, “Diane,” she began,” I think we would like to borrow some of Bobby’s things after all! Perhaps Daphne would be willing to help us choose something appropriate!”
Diane Green nodded curtly and replied at once, “Of course, and if I may say so, it’s not a moment too soon!”
Jason froze, and his heart pounded fiercely in his chest. He realized he had really stepped into it now! He heard Daphne speak next to his mother, “Oh I’d be happy to help with your little mischief-maker, Mrs. Thomas!” She added, “I think that gorgeous blue party dress and Mary Janes that Bobby wore last time will fit Jason nicely, and I’ll get him a pretty pair of ruffled panties too!”
Mrs. Thomas looked at her smart-mouthed son with satisfaction. She couldn’t wait to put him into the petticoats he had so richly earned!
Bobby and Jamie looked on with embarrassed sympathy, and it made them feel even more defeated to know that another classmate would soon join them in petticoats. It all seemed so overwhelming and inescapable to them now.
An instant later, Jason found himself being frogmarched out of the room by his mother and Daphne as all the ladies in the book club looked on. They seemed very pleased that this lippy, misbehaving teenager would soon learn the error of his ways! Jason’s emotions were all over the place as he realized he would soon follow his classmates into a sea of feminine dresses and petticoats. It was almost too much for him to process. His tummy was doing backflips, and he felt swept along by this sudden turn of events.
The whole situation just felt so absurd… and magical! Flabbergasted, Jason couldn’t believe what he had just done. It had worked! He was almost beside himself as he eagerly imagined what his dress would look like! And panties too! He was afraid he had been too obvious about it, but now it was really happening. He wasn’t exactly sure what he had gotten himself into, but his heart told him he was going to like it. Either way, it was too late to turn back!
Ever since his mother had explained petticoating on the car ride over, he had been almost obsessed with the idea. It sounded wonderful to him! He was still hesitant to admit the truth to himself, but it appeared he had played his cards just right. Fate had presented him the perfect excuse to finally try something he’d thought about forever! Doing it this way, he reasoned, he could keep his true desires secret and still get to take part in this marvelous adventure! He reminded himself that he’d have to act reluctant, but he felt like jumping for joy! He couldn’t wait to get his very own petticoat and dress! He tried to imagine how it would feel to have his hair put into adorable ringlet curls just like Jamie! Jason was ecstatic to be joining his friends and starting his own Petticoating Journey. He was practically trembling with excitement!
Meanwhile, all the ladies of the book club tittered with appreciation as they watched Jason get escorted expeditiously from the room. They couldn’t wait to see how his attitude changed once he was securely buttoned into his lovely frock and petticoat. Another unruly young lad would soon get his well-deserved comeuppance!
Diane Green, however, had a curious look on her face. She had a different feeling altogether about what had just occurred. As she had observed Jason get ushered out by Abigail and Daphne to be put into his first dress and petticoat, she was nearly certain she had detected a fleeting flash of… delight, perhaps? As she replayed the last few moments in her mind, she felt that something was off. The more she thought about it, the entire episode felt… contrived. Then, she reached a sudden realization. It felt contrived because it was!
“That little rascal!” Diane thought to herself with a chuckle. It dawned on her that they had all been treated to a clever little acting job. There was apparently much more to this Jason Thomas than met the eye. In fact, after seeing that performance, she now thought he might be precocious. For an instant, however, he had let his mask slip. Unless she was badly mistaken, she had stumbled upon a Natural Sissy! If that was true, Jason already stood on the doorstep of the Appreciation stage of Petticoating. He just needed the tiniest nudge to admit it and tumble through the door! Now she felt that she fully understood the situation. Understandably, Jason was likely still afraid to embrace his true nature, and he didn’t know how to handle his feelings. Society said that boys shouldn’t want such things, so he was hiding. His deceptive outburst was merely a cry for help. It seemed obvious now that he longed for the structure and comfort of petticoats!
Of course, she’d need to confirm her suspicions, but that should be easy enough. She could set some simple traps, and she felt certain young Jason would eagerly take the bait and reveal his true self! She would just provide him a few obvious opportunities to avoid Petticoating. After he got his first taste of dresses and petticoats, Diane was confident that he would practically contort himself into a pretzel to hold onto them!
Natural Sissies were not exactly rare, but they certainly comprised only a small minority of boys. Once she knew for sure, she would need to guide Abigail carefully. The boy was clearly intelligent… and also crafty. His mother was well-intentioned, but it appeared he had just played her like a fiddle!
Jason presented a different type of challenge, and his progression would require a more nuanced approach than either Bobby or Jamie. The normal rules of Petticoating did not apply to Natural Sissies, so Jason’s Petticoating Journey would have to follow a much different path than his classmates. In fact, “Petticoat Punishment” was a misnomer for boys like Jason, since true punishment would be taking his petticoats away! Still, having a Natural Sissy in the mix presented an enormous opportunity! As a role model, Jason could prove quite helpful in cementing permanent behavior changes in his little friends!
“I’ll return in a moment, ladies, and then we can finally begin our book discussion,” Diane told the rest of the club. She added cheerily, “I just want to make sure that Abigail and Daphne have all they need to get young Master Jason properly sorted out!” As she left the great room, her mind buzzed with new possibilities.
“What a wonderful turn of events,” she thought to herself, “Jason Thomas has no idea how lucky he is, but he will soon find out!” With amusement, she thought, “I won’t make it too easy on him, though, after that sneaky little ruse!” While Jason was clearly mesmerized by the idea of petticoating, he was clueless as to what it would entail in practice. Still, she couldn’t wait to begin molding him into a delightfully girlish model of Petticoating Success! Once he accepted his true nature, she was certain he would enthusiastically take to his dresses like a duck to water!
Diane also suspected it would all happen very swiftly. She predicted his little charade would soon collapse like a house of cards! Perhaps she should encourage Abigail to begin Fulltime Petticoating immediately? That might be best for everyone. “Even if he’s a Natural Sissy, I bet he won’t expect THAT!” she thought with amusement. After the initial shock to his system, however, she was confident Jason would eagerly embrace his new life!
Her imagination ran wild as she pictured ever more dainty and feminine outfits for all three of the boys! She even recalled reading on one of the petticoating forums she had joined about an exclusive group of mothers who occasionally held private Petticoat Pageants. The pageants provided wonderful opportunities to network with like-minded mothers, and they recognized Petticoating success stories. Of course, they were only open to the most thoroughly petticoated boys. As a minimum, boys had to have reached Compliance but preferably attained the more advanced stages of Acceptance or Appreciation. Perhaps that was now a realistic possibility for all three of their petticoated teens!
As she entered the other room, she saw that Daphne had already retrieved the toddlerish blue party dress and shiny black Mary Janes for her newest charge. Upon noting Jason’s reaction, she was now convinced her suspicions were correct. While Jamie and Bobby still looked miserably meek in their sissified tulle dresses, Jason couldn’t help himself. He was absolutely spellbound by the exquisitely girlish dress he would soon be wearing. The look of anticipation on his face was just precious as he eyed its gorgeous details. He was positively giddy! Once you knew what to look for, the signs of a Natural Sissy were unmistakable! Diane had his number now, and she took charge.
“Oh Abigail,” Diane called gaily, “could I speak to you in private for just a moment?” Next, she directed her son, “Bobby, go fetch that darling pink nail polish from Mommy’s dressing table so you can paint Jason’s nails… I think it will be fun to do that in front of the book club while we have our discussion!” Lastly, she added mischievously in a somewhat exaggerated tone, “and Daphne, be sure to get our dear little Jason a nice, frilly petticoat to wear with his pretty party dress!”
As Diane watched, Jason’s eyes lit up brightly and he shuddered involuntarily. She couldn't help giggling at the sight. Poor thing! Precocious or not, Natural Sissies became so predictable when you knew what buttons to push!
THE END
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Truly a brilliant story! I’m so glad you’re back writing! I hope to hear how Clarissa has been?
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sissyboy1212, Thank you for the wonderful story.
As for Jason, it appears this will not be a punishment. But, if there is a need to "take him down a peg or two" he could be introduced to another aspect of petty-coating. Pampers, Luvs, and Huggies now go up to size 8. Some pretty ruffled panties can still cover the diapers. Unfortunately, this story has ended, and we will not be introduced to a diapered Jason.
Again thank you for the time and effort to put together such a wonderful story.
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Thank you gunrunner, Norm43 and the handful of others who left encouraging comments. I'm glad you enjoyed it!
I also want to give a special shout out to Princess PowderPuff for your wonderful story “A Sissy is Born.” There are certainly elements in Jamie’s story that were inspired by that. Thank you for sharing!
And to gunrunner: While this story is indeed over, I'm always open to revisiting characters if I can think of something interesting to do with them... or to them!
Thanks again and Happy New Year!
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I gotta say, the way you write and your details are incredible. Pretty pretty please write a story about the Ballet Class. It’s so rare to see a very well done ballet story done.
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Thank you gunrunner, Norm43 and the handful of others who left encouraging comments. I'm glad you enjoyed it!
I also want to give a special shout out to Princess PowderPuff for your wonderful story “A Sissy is Born.” There are certainly elements in Jamie’s story that were inspired by that. Thank you for sharing!
And to gunrunner: While this story is indeed over, I'm always open to revisiting characters if I can think of something interesting to do with them... or to them!
Thanks again and Happy New Year!
You are so welcome and thank you for your kind words. I thoroughly enjoyed your story and it's nice to know that in some small way that "A Sissy is Born" inspired elements of your story and it has encouraged me to work on completing my story. All I need to do now is tame the tremors in my right arm and we're cookin'.
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Thank you so much for the story.
I really enjoied the phase of sissy boy wearing bow tie and apron.
I will be so glad if there will be a story where sporty boy football player slowly turning by his mommy to weak sissy. Forst from tshirts and jeans to dressy shirts buttoned up to the top and dressy shorts. The. The shorts become ahorter and dressier and more infant style. The shirt get puffy sleeve and necktie is added. Less grown up actovities the. Nexktie replaced by bow and hairboq is added etc.
Also the addition of another boy that pass the same events and reluctantly dressing up his friend is great.
I wish i had timw to write it myself but the events now in my life.prevents me....
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You are so welcome and thank you for your kind words. I thoroughly enjoyed your story and it's nice to know that in some small way that "A Sissy is Born" inspired elements of your story and it has encouraged me to work on completing my story. All I need to do now is tame the tremors in my right arm and we're cookin'.
Best of luck as you work through the challenges of life and look forward to reading more. I just love the early chapters of your story where David is zipped into his “sissy salon sack” and securely strapped in to get his hair curled and full sissy makeover done!
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Sissyboy, thank you for finishing the wonderful story. I have just finished reading it for the second time and am wondering if there might be a story of Jason's adventures with Jamie and Bobby. As it has been suggested Jason may be a willing participant in his own sissification but will that willingness help the ladies speed up the plans for his classmates and will other boys be drawn into the web cast by these determined ladies.
SissyBallerina Boy asked if their could be story about the ballet class. I would love to read such a story as they are few and far between, especially good ones with your writing style.
Once again, thank you for your stories.